JP2005538152A - ジアリール誘導体及びこれをクロライドチャネル遮断剤として使用する方法 - Google Patents
ジアリール誘導体及びこれをクロライドチャネル遮断剤として使用する方法 Download PDFInfo
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- JP2005538152A JP2005538152A JP2004533214A JP2004533214A JP2005538152A JP 2005538152 A JP2005538152 A JP 2005538152A JP 2004533214 A JP2004533214 A JP 2004533214A JP 2004533214 A JP2004533214 A JP 2004533214A JP 2005538152 A JP2005538152 A JP 2005538152A
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- Prior art keywords
- phenyl
- ureido
- urea
- chloro
- tetrazol
- Prior art date
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- 108010062745 Chloride Channels Proteins 0.000 title claims abstract description 26
- 102000011045 Chloride Channels Human genes 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 25
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 161
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 79
- 201000010099 disease Diseases 0.000 claims abstract description 46
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 210000003651 basophil Anatomy 0.000 claims abstract description 13
- 210000003630 histaminocyte Anatomy 0.000 claims abstract description 13
- 210000000988 bone and bone Anatomy 0.000 claims abstract description 12
- 230000000694 effects Effects 0.000 claims abstract description 11
- 230000014399 negative regulation of angiogenesis Effects 0.000 claims abstract description 8
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 5
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- -1 cyclohexanyl Chemical group 0.000 claims description 470
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 328
- 239000004202 carbamide Substances 0.000 claims description 211
- 239000001257 hydrogen Substances 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 72
- 125000005843 halogen group Chemical group 0.000 claims description 67
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 37
- 208000035475 disorder Diseases 0.000 claims description 33
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 32
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 30
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 27
- 125000004122 cyclic group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- RISYHVKNVBDQKU-UHFFFAOYSA-N 2-amino-3-oxoprop-2-enoic acid Chemical compound O=C=C(N)C(O)=O RISYHVKNVBDQKU-UHFFFAOYSA-N 0.000 claims description 15
- 239000005711 Benzoic acid Substances 0.000 claims description 15
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 208000006673 asthma Diseases 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 229960002449 glycine Drugs 0.000 claims description 12
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 9
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 9
- 208000002780 macular degeneration Diseases 0.000 claims description 9
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
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- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 210000002997 osteoclast Anatomy 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- DYULFVSZYBKRCA-UHFFFAOYSA-N 1-[4-chloro-2-(dimethoxyphosphorylmethyl)phenyl]-3-(3,4-dichlorophenyl)urea Chemical compound COP(=O)(OC)CC1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 DYULFVSZYBKRCA-UHFFFAOYSA-N 0.000 claims description 6
- KWOSFTHPUFTQSO-UHFFFAOYSA-N 2-[(2,6-dichloropyridin-4-yl)carbamoylamino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1NC(=O)NC1=CC(Cl)=NC(Cl)=C1 KWOSFTHPUFTQSO-UHFFFAOYSA-N 0.000 claims description 6
- 206010006474 Bronchopulmonary aspergillosis allergic Diseases 0.000 claims description 6
- 206010012434 Dermatitis allergic Diseases 0.000 claims description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- 208000006778 allergic bronchopulmonary aspergillosis Diseases 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- VXEQMJBWIDUNIS-UHFFFAOYSA-N 3,5-bis[[3,5-bis(trifluoromethyl)phenyl]carbamoylamino]benzoic acid Chemical compound C=1C(NC(=O)NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=CC(C(=O)O)=CC=1NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VXEQMJBWIDUNIS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 208000020084 Bone disease Diseases 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 230000001066 destructive effect Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 210000001519 tissue Anatomy 0.000 claims description 4
- KSEPXZUDENGCBK-UHFFFAOYSA-N 1-(2,3-difluorophenyl)-3-pyridin-3-ylurea Chemical compound FC1=CC=CC(NC(=O)NC=2C=NC=CC=2)=C1F KSEPXZUDENGCBK-UHFFFAOYSA-N 0.000 claims description 3
- KAHLMJSOSXKFJU-UHFFFAOYSA-N 1-(2,3-difluorophenyl)-3-pyridin-4-ylurea Chemical compound FC1=CC=CC(NC(=O)NC=2C=CN=CC=2)=C1F KAHLMJSOSXKFJU-UHFFFAOYSA-N 0.000 claims description 3
- GUGYTOAADAMCQI-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[2,4-dichloro-6-(2h-tetrazol-5-yl)phenyl]urea Chemical compound N=1N=NNC=1C1=CC(Cl)=CC(Cl)=C1NC(=O)NC1=C(Cl)C=CC=C1Cl GUGYTOAADAMCQI-UHFFFAOYSA-N 0.000 claims description 3
- CGDQVTUJRGGRCD-UHFFFAOYSA-N 1-(2,6-dichloropyridin-4-yl)-3-(2-diethoxyphosphorylphenyl)urea Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1NC(=O)NC1=CC(Cl)=NC(Cl)=C1 CGDQVTUJRGGRCD-UHFFFAOYSA-N 0.000 claims description 3
- POLSPLRLJQIMNB-UHFFFAOYSA-N 1-(2,6-dichloropyridin-4-yl)-3-[2,3-difluoro-4-(trifluoromethyl)phenyl]urea Chemical compound FC1=C(F)C(C(F)(F)F)=CC=C1NC(=O)NC1=CC(Cl)=NC(Cl)=C1 POLSPLRLJQIMNB-UHFFFAOYSA-N 0.000 claims description 3
- PUYQKSHYTVOJBH-UHFFFAOYSA-N 1-(2-diethoxyphosphorylphenyl)-3-[2-(trifluoromethyl)phenyl]urea Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F PUYQKSHYTVOJBH-UHFFFAOYSA-N 0.000 claims description 3
- NLGDRSKAJWBABR-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-(2-diethoxyphosphorylphenyl)urea Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 NLGDRSKAJWBABR-UHFFFAOYSA-N 0.000 claims description 3
- VCKDDIDEVBXDAE-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[2,4-dichloro-6-(2h-tetrazol-5-yl)phenyl]urea Chemical compound ClC1=CC(Cl)=CC(NC(=O)NC=2C(=CC(Cl)=CC=2Cl)C=2NN=NN=2)=C1 VCKDDIDEVBXDAE-UHFFFAOYSA-N 0.000 claims description 3
- WJMJEWOSMJNPLX-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-[4-(piperidine-1-carbonyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound ClC1=CC(Cl)=CC(NC(=O)NC=2C(=CC(=CC=2)C(=O)N2CCCCC2)C=2NN=NN=2)=C1 WJMJEWOSMJNPLX-UHFFFAOYSA-N 0.000 claims description 3
- XZZDZPNPSNBWCX-UHFFFAOYSA-N 1-(3,5-difluorophenyl)-3-[4-(piperidine-1-carbonyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound FC1=CC(F)=CC(NC(=O)NC=2C(=CC(=CC=2)C(=O)N2CCCCC2)C=2NN=NN=2)=C1 XZZDZPNPSNBWCX-UHFFFAOYSA-N 0.000 claims description 3
- IIXKMDVMIRZMLO-UHFFFAOYSA-N 1-(3-bromophenyl)-3-(2-diethoxyphosphorylphenyl)urea Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1NC(=O)NC1=CC=CC(Br)=C1 IIXKMDVMIRZMLO-UHFFFAOYSA-N 0.000 claims description 3
- KPIUSQVXLDOKOG-UHFFFAOYSA-N 1-(3-bromophenyl)-3-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound C=1C=CC(Br)=CC=1NC(=O)NC1=CC(Cl)=CC=C1C1=NN=NN1 KPIUSQVXLDOKOG-UHFFFAOYSA-N 0.000 claims description 3
- DDCUBKOUNSXEOL-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound ClC1=CC=CC(NC(=O)NC=2C(=CC=C(Cl)C=2)C=2NN=NN=2)=C1 DDCUBKOUNSXEOL-UHFFFAOYSA-N 0.000 claims description 3
- WUWUTZBHKMSYRI-UHFFFAOYSA-N 1-(4-bromo-2-diethoxyphosphorylphenyl)-3-(3,5-dichlorophenyl)urea Chemical compound CCOP(=O)(OCC)C1=CC(Br)=CC=C1NC(=O)NC1=CC(Cl)=CC(Cl)=C1 WUWUTZBHKMSYRI-UHFFFAOYSA-N 0.000 claims description 3
- SMSAZCHOFLMBTC-UHFFFAOYSA-N 1-(4-bromo-2-diethoxyphosphorylphenyl)-3-(3-bromophenyl)urea Chemical compound CCOP(=O)(OCC)C1=CC(Br)=CC=C1NC(=O)NC1=CC=CC(Br)=C1 SMSAZCHOFLMBTC-UHFFFAOYSA-N 0.000 claims description 3
- RPJFRZCQABCFPQ-UHFFFAOYSA-N 1-(4-bromo-2-diethoxyphosphorylphenyl)-3-(3-chlorophenyl)urea Chemical compound CCOP(=O)(OCC)C1=CC(Br)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 RPJFRZCQABCFPQ-UHFFFAOYSA-N 0.000 claims description 3
- ZYKQNIZZWLCZIY-UHFFFAOYSA-N 1-(4-bromo-2-diethoxyphosphorylphenyl)-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound CCOP(=O)(OCC)C1=CC(Br)=CC=C1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 ZYKQNIZZWLCZIY-UHFFFAOYSA-N 0.000 claims description 3
- MCMRHIIVSHWBEA-UHFFFAOYSA-N 1-(cyclohexylcarbamoyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCCN1C(=O)NC1CCCCC1 MCMRHIIVSHWBEA-UHFFFAOYSA-N 0.000 claims description 3
- QQBIKMKKCPPMIU-UHFFFAOYSA-N 1-(pyridin-3-ylcarbamoyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCCN1C(=O)NC1=CC=CN=C1 QQBIKMKKCPPMIU-UHFFFAOYSA-N 0.000 claims description 3
- PDSYQASAEPXSCR-UHFFFAOYSA-N 1-[(2,6-dichloropyridin-4-yl)carbamoyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCCN1C(=O)NC1=CC(Cl)=NC(Cl)=C1 PDSYQASAEPXSCR-UHFFFAOYSA-N 0.000 claims description 3
- HXGWUHJVXPKVEB-UHFFFAOYSA-N 1-[(3,5-dichlorophenyl)carbamoyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCCN1C(=O)NC1=CC(Cl)=CC(Cl)=C1 HXGWUHJVXPKVEB-UHFFFAOYSA-N 0.000 claims description 3
- VTRZSCNVLAFWEV-UHFFFAOYSA-N 1-[(3-bromophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carboxylic acid Chemical compound C1C(O)CC(C(O)=O)N1C(=O)NC1=CC=CC(Br)=C1 VTRZSCNVLAFWEV-UHFFFAOYSA-N 0.000 claims description 3
- SUTKLGVVBDABFO-UHFFFAOYSA-N 1-[(3-bromophenyl)carbamoyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCCN1C(=O)NC1=CC=CC(Br)=C1 SUTKLGVVBDABFO-UHFFFAOYSA-N 0.000 claims description 3
- LYXDOHLUDPXZFM-UHFFFAOYSA-N 1-[(3-chlorophenyl)carbamoyl]-4-hydroxypyrrolidine-2-carboxylic acid Chemical compound C1C(O)CC(C(O)=O)N1C(=O)NC1=CC=CC(Cl)=C1 LYXDOHLUDPXZFM-UHFFFAOYSA-N 0.000 claims description 3
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- YQUBLNQICXKOSZ-UHFFFAOYSA-N 1-[2,3-difluoro-4-(trifluoromethyl)phenyl]-3-pyridin-3-ylurea Chemical compound C1=CC(C(F)(F)F)=C(F)C(F)=C1NC(=O)NC1=CC=CN=C1 YQUBLNQICXKOSZ-UHFFFAOYSA-N 0.000 claims description 3
- AROHFDUUTGBAMH-UHFFFAOYSA-N 1-[2,3-difluoro-4-(trifluoromethyl)phenyl]-3-pyridin-4-ylurea Chemical compound C1=CC(C(F)(F)F)=C(F)C(F)=C1NC(=O)NC1=CC=NC=C1 AROHFDUUTGBAMH-UHFFFAOYSA-N 0.000 claims description 3
- HJQLALJBZFTTLC-UHFFFAOYSA-N 1-[2,4-dibromo-6-(2h-tetrazol-5-yl)phenyl]-3-(2,6-dichloropyridin-4-yl)urea Chemical compound ClC1=NC(Cl)=CC(NC(=O)NC=2C(=CC(Br)=CC=2Br)C=2NN=NN=2)=C1 HJQLALJBZFTTLC-UHFFFAOYSA-N 0.000 claims description 3
- KCPGHJZBOMUMPP-UHFFFAOYSA-N 1-[2,4-dibromo-6-(2h-tetrazol-5-yl)phenyl]-3-(3,4-dichlorophenyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=C(Br)C=C(Br)C=C1C1=NN=NN1 KCPGHJZBOMUMPP-UHFFFAOYSA-N 0.000 claims description 3
- HWLFEFFGCSBQTA-UHFFFAOYSA-N 1-[2,4-dibromo-6-(2h-tetrazol-5-yl)phenyl]-3-(3,5-dichlorophenyl)urea Chemical compound ClC1=CC(Cl)=CC(NC(=O)NC=2C(=CC(Br)=CC=2Br)C=2NN=NN=2)=C1 HWLFEFFGCSBQTA-UHFFFAOYSA-N 0.000 claims description 3
- GTDFKKRKMVYXSB-UHFFFAOYSA-N 1-[2,4-dibromo-6-(2h-tetrazol-5-yl)phenyl]-3-[4-fluoro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC1=C(Br)C=C(Br)C=C1C1=NN=NN1 GTDFKKRKMVYXSB-UHFFFAOYSA-N 0.000 claims description 3
- KKEWOOLOHOTVPM-UHFFFAOYSA-N 1-[2,4-dichloro-6-(2h-tetrazol-5-yl)phenyl]-3-(2,4,6-trichlorophenyl)urea Chemical compound ClC1=CC(Cl)=CC(Cl)=C1NC(=O)NC1=C(Cl)C=C(Cl)C=C1C1=NN=NN1 KKEWOOLOHOTVPM-UHFFFAOYSA-N 0.000 claims description 3
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- DJCXVPMXUKFZRE-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-(2-diethoxyphosphorylphenyl)urea Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DJCXVPMXUKFZRE-UHFFFAOYSA-N 0.000 claims description 3
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- WGELTVGQMVGQPS-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2,6-dibromo-3-(2h-tetrazol-5-yl)phenyl]urea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC=2C(=C(C=3NN=NN=3)C=CC=2Br)Br)=C1 WGELTVGQMVGQPS-UHFFFAOYSA-N 0.000 claims description 3
- HFKBAHZDEWBULQ-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-bromo-5-(2h-tetrazol-5-yl)phenyl]urea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC=2C(=CC=C(C=2)C=2NN=NN=2)Br)=C1 HFKBAHZDEWBULQ-UHFFFAOYSA-N 0.000 claims description 3
- XWIVGRZHFVCCOJ-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[4-(piperidine-1-carbonyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC=2C(=CC(=CC=2)C(=O)N2CCCCC2)C=2NN=NN=2)=C1 XWIVGRZHFVCCOJ-UHFFFAOYSA-N 0.000 claims description 3
- XDZFOVZZEXUDFQ-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[5-chloro-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC=2C(=CC=C(Cl)C=2)C=2NN=NN=2)=C1 XDZFOVZZEXUDFQ-UHFFFAOYSA-N 0.000 claims description 3
- PAYBCWBFPFUPEF-UHFFFAOYSA-N 1-[4-bromo-2-(2h-tetrazol-5-yl)phenyl]-3-(2,6-dichloropyridin-4-yl)urea Chemical compound ClC1=NC(Cl)=CC(NC(=O)NC=2C(=CC(Br)=CC=2)C=2NN=NN=2)=C1 PAYBCWBFPFUPEF-UHFFFAOYSA-N 0.000 claims description 3
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- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA200201306 | 2002-09-05 | ||
DKPA200201310 | 2002-09-05 | ||
PCT/DK2003/000575 WO2004022529A2 (fr) | 2002-09-05 | 2003-09-04 | Derives de diaryluree et leur utilisation comme bloqueurs de canaux chlorure |
Publications (1)
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JP2005538152A true JP2005538152A (ja) | 2005-12-15 |
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JP2004533214A Pending JP2005538152A (ja) | 2002-09-05 | 2003-09-04 | ジアリール誘導体及びこれをクロライドチャネル遮断剤として使用する方法 |
Country Status (10)
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US (1) | US20060160856A1 (fr) |
EP (1) | EP1537075B1 (fr) |
JP (1) | JP2005538152A (fr) |
CN (1) | CN100497302C (fr) |
AT (1) | ATE435199T1 (fr) |
CA (1) | CA2495284A1 (fr) |
DE (1) | DE60328202D1 (fr) |
MX (1) | MXPA05002493A (fr) |
NZ (1) | NZ538513A (fr) |
WO (1) | WO2004022529A2 (fr) |
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Cited By (18)
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WO2010125799A1 (fr) * | 2009-04-27 | 2010-11-04 | 塩野義製薬株式会社 | Dérivé d'urée présentant une activité inhibitrice de la pi3k |
US10993931B2 (en) | 2011-10-26 | 2021-05-04 | Allergan, Inc. | Amide derivatives of N-urea substituted amino acids as formyl peptide receptor like-1 (FPRL-1) receptor modulators |
US10899780B2 (en) | 2013-03-06 | 2021-01-26 | Allergan, Inc. | Use of agonists of formyl peptide receptor 2 for treating ocular inflammatory diseases |
JP2019108391A (ja) * | 2013-03-06 | 2019-07-04 | アラーガン、インコーポレイテッドAllergan,Incorporated | 皮膚疾患を治療するためのホルミルペプチド受容体2アゴニストの使用 |
JP2017214418A (ja) * | 2013-03-06 | 2017-12-07 | アラーガン、インコーポレイテッドAllergan,Incorporated | 皮膚疾患を治療するためのホルミルペプチド受容体2アゴニストの使用 |
JP2017214417A (ja) * | 2013-03-06 | 2017-12-07 | アラーガン、インコーポレイテッドAllergan,Incorporated | 皮膚疾患を治療するためのホルミルペプチド受容体2アゴニストの使用 |
JP2018009012A (ja) * | 2013-03-06 | 2018-01-18 | アラーガン、インコーポレイテッドAllergan,Incorporated | 眼炎症性疾患の治療のためのホルミルペプチド受容体2のアゴニストの使用 |
US10208071B2 (en) | 2013-03-06 | 2019-02-19 | Allergan, Inc. | Use of agonists of formyl peptide receptor 2 for treating ocular inflammatory diseases |
JP2016512193A (ja) * | 2013-03-06 | 2016-04-25 | アラーガン、インコーポレイテッドAllergan,Incorporated | 眼炎症性疾患の治療のためのホルミルペプチド受容体2のアゴニストの使用 |
JP2017214416A (ja) * | 2013-03-06 | 2017-12-07 | アラーガン、インコーポレイテッドAllergan,Incorporated | 眼炎症性疾患の治療のためのホルミルペプチド受容体2のアゴニストの使用 |
JP2016512194A (ja) * | 2013-03-06 | 2016-04-25 | アラーガン、インコーポレイテッドAllergan,Incorporated | 皮膚疾患を治療するためのホルミルペプチド受容体2アゴニストの使用 |
JP2019131569A (ja) * | 2013-03-06 | 2019-08-08 | アラーガン、インコーポレイテッドAllergan,Incorporated | 眼炎症性疾患の治療のためのホルミルペプチド受容体2のアゴニストの使用 |
JP2019509313A (ja) * | 2016-03-24 | 2019-04-04 | アジエンダ・オスペダリエラ・ウニベルシタリア・セネーゼ | 抗増殖剤としてのddx3阻害剤の使用 |
JP7073269B2 (ja) | 2016-03-24 | 2022-05-23 | アジエンダ・オスペダリエラ・ウニベルシタリア・セネーゼ | 抗増殖剤としてのddx3阻害剤の使用 |
JP2019520359A (ja) * | 2016-06-22 | 2019-07-18 | フーダン ユニヴァーシティFudan University | ビアリール尿素誘導体またはそれらの塩、およびそれらの調製方法および使用 |
JP7092356B2 (ja) | 2016-06-22 | 2022-06-28 | フーダン ユニヴァーシティ | ビアリール尿素誘導体またはそれらの塩、およびそれらの調製方法および使用 |
JP2021024832A (ja) * | 2019-08-07 | 2021-02-22 | 国立大学法人東北大学 | ジフェニル尿素化合物誘導体 |
JP7336133B2 (ja) | 2019-08-07 | 2023-08-31 | 国立大学法人東北大学 | ジフェニル尿素化合物誘導体 |
Also Published As
Publication number | Publication date |
---|---|
EP1537075B1 (fr) | 2009-07-01 |
EP1537075A2 (fr) | 2005-06-08 |
ATE435199T1 (de) | 2009-07-15 |
WO2004022529A3 (fr) | 2004-05-13 |
AU2003258490A1 (en) | 2004-03-29 |
NZ538513A (en) | 2007-02-23 |
CA2495284A1 (fr) | 2004-03-18 |
US20060160856A1 (en) | 2006-07-20 |
DE60328202D1 (de) | 2009-08-13 |
CN1678573A (zh) | 2005-10-05 |
WO2004022529A2 (fr) | 2004-03-18 |
MXPA05002493A (es) | 2005-05-27 |
CN100497302C (zh) | 2009-06-10 |
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